EP0719278A1 - Androstenderivate - Google Patents
AndrostenderivateInfo
- Publication number
- EP0719278A1 EP0719278A1 EP94929828A EP94929828A EP0719278A1 EP 0719278 A1 EP0719278 A1 EP 0719278A1 EP 94929828 A EP94929828 A EP 94929828A EP 94929828 A EP94929828 A EP 94929828A EP 0719278 A1 EP0719278 A1 EP 0719278A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- formula
- solvate
- bis
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/82—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0066—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by a carbon atom forming part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/005—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by nitrogen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
Definitions
- the present invention relates to a particular 17 ⁇ -anilide-4-aza-5 ⁇ -androst-1- en-3-one derivative, as a surprisingly potent and selective dual inhibitor of type 1 and 2 human 5 ⁇ -reductase.
- Androgens are responsible for many physiological functions in both males and females. Androgen action is mediated by specific intracellular hormone receptors expressed in androgen responsive cells. Testosterone, the major circulating androgen, is secreted by Leydig cells of the testes under the stimulation of pituitary-derived luteinizing hormone (LH). However, reduction of the 4, 5 double bond of testosterone to dihydrotestosterone (DHT) is required in some target tissues, such as prostate and skin, for androgen action. Steroid 5 ⁇ -reductases in target tissues catalyze conversion of testosterone to DHT in an NADPH dependent fashion as shown in Scheme A.
- DHT dihydrotestosterone
- isozyme specific and dual inhibitors of the two isozymes of 5 ⁇ -reductase will depend upon the type of disease treated (benign prostatic hyperplasia, prostate cancer, acne, male pattern baldness or hirsutism) as well as the stage of the disease (prevention versus treatment) and the anticipated side-effects in the intended patients (for example treatment of acne vulgaris in pubescent males).
- H 5 ⁇ -reductase inhibitors have been the subject of active research worldwide. For example, see: Hsia, S. and Voight, W., J. Invest. Derm., 62, 224 (1973); Robaire, B. et al., J. Steroid Biochem., 8, 307 (1977); Petrow, V. et al., Steroids, 38, 121 (1981); Liang, T. et al., J. Steroid Biochem., 19, 385 (1983); Holt, D. et al., J. Med. Chem., 33, 937 (1990); U.S. Patent No.
- One aspect of the present invention is the compound of formula (I),
- a method of inhibiting testosterone-5 ⁇ -reductases comprising contacting testosterone-5 ⁇ -reductases with the compound of formula (I). 2. A method of treatment of androgen responsive or mediated disease comprising administering an effective amount of the compound of formula (I) to a patient in need of such treatment.
- a method of treatment of androgen responsive or mediated disease comprising administering an effective amount of the compound of formula (I) to a patient in need of such treatment in combination with an antiandrogen such as flutamide.
- a method of treatment of benign prostatic hyperplasia comprising administering an effective amount of the compound of formula (I) to a patient in need of such treatment in combination with an alpha 1 adrenergic receptor blocker ⁇ e.g. terazosin).
- an alpha 1 adrenergic receptor blocker ⁇ e.g. terazosin
- a method of treatment of benign prostatic hyperplasia comprising administering an effective amount of the compound of formula (I) to a patient in need of such treatment in combination with an anti-estrogen.
- the compound of the present invention may be prepared by the methods taught in US Patents 4,377,584 (hereinafter, , "584") and 4,760,071 (hereinafter, "O71") both incorporated herein by reference.
- the compound of formula (I) may be prepared by the procedure shown in Scheme I and II.
- Enzyme activities are measured using microsomes derived from human adrenal tissues. Microsomes were prepared by homogenization of the tissue followed by differential centrifugation of the homogenate. Microsome extracts were incubated with varying concentrations of dehydroepiandrosterone (DHEA), 1 mM NAD+- and varying amounts of the compound of Formula (I), i.e. a test compound, in pH 7.5 buffer for a period of time within the range of 1 to 60 minutes. Corresponding incubations were carried out with no test compound as a control study. The percentage of conversion of DHEA to androstenedione in the presence of test compounds compared to the corresponding conversion in the control study was estimated using HPLC with radiochemical detection. The results of these assays appear as Kj's reported in Table 1.
- the steroid 5 ⁇ -reductase inhibitor of the present invention is useful in the treatment of androgen responsive diseases , e.g., benign and malignant diseases of the prostate, especially benign prostatic hyperplasia, in a manner similar to that for other 5 ⁇ -reductase inhibitors such as finasteride and SKF105657.
- the compound of the present invention has a surprisingly long half-life and potency compared to finasteride and SKF105657.
- the formulations may conveniently be presented in unit dosage form and may be prepared by any of the methods well known in the art of pharmacy. All methods include the step of bringing the active compound into association with a carrier which constitutes one or more accessory ingredients. In general, the formulations are prepared by uniformly and intimately bringing the active compound into association with a liquid carrier or a finely divided solid carrier and then, if necessary, shaping the product into desired unit dosage form.
- a tablet may be made by compression or molding, optionally with one or more accessory ingredients.
- Compressed tablets may be prepared by compressing in a suitable machine the active compound in a free-flowing form, e.g., a powder or granules, optionally mixed with accessory ingredients, e.g., binders, lubricants, inert diluents, surface active or dispersing agents.
- Molded tablets may be made by molding in a suitable machine, a mixture of the powdered active compound with any suitable carrier.
- reaction mixture is filtered through a bed of celite (50 g) and the solid is washed with water and the filtrate concentrated in vacuo to remove f-butanol (ca. 175 ml).
- the resultant aqueous solution is acidified to pH 2 with 36% HCI and the extracted 4 times with chloroform.
- the chloroform layers are combined and washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 17 ⁇ -N-(2,5-bis(trifluoromethyl))phenylcarbamoyl-5-oxo-A-nor-3,5-secoandros- tan-3-oic acid as a off-white solid; yield: 20.5 g (100% crude). This material is carried directly into step C below.
- the silicone fluid and active compound are mixed together and the colloidal silicone dioxide is added to increase viscosity.
- the material is then dosed into a subsequently heat sealed polymeric laminate comprised of the following: polyester release liner, skin contact adhesive composed of silicone or acrylic polymers, a control membrane which is a polyolefin ⁇ e.g. polyethylene, polyvinyl acetate or polyurethane), and an impermeable backing membrane made of a polyester multilaminate.
- the resulting laminated sheet is then cut into 10 sq. cm patches.
- the active compound and the starch are granulated with water and dried. Magnesium stearate is added to the dried granules and the mixture is thoroughly blended. The blended mixture is compressed into tablets.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SI9430130T SI0719278T1 (en) | 1993-09-17 | 1994-09-16 | Androstenone derivative |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12328093A | 1993-09-17 | 1993-09-17 | |
US123280 | 1993-09-17 | ||
PCT/US1994/010530 WO1995007927A1 (en) | 1993-09-17 | 1994-09-16 | Androstenone derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0719278A1 true EP0719278A1 (de) | 1996-07-03 |
EP0719278B1 EP0719278B1 (de) | 1998-01-14 |
Family
ID=22407744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94929828A Expired - Lifetime EP0719278B1 (de) | 1993-09-17 | 1994-09-16 | Androstenderivate |
Country Status (41)
Country | Link |
---|---|
US (2) | US5565467A (de) |
EP (1) | EP0719278B1 (de) |
JP (1) | JP2904310B2 (de) |
KR (1) | KR100364953B1 (de) |
CN (1) | CN1057771C (de) |
AP (1) | AP494A (de) |
AT (1) | ATE162199T1 (de) |
AU (1) | AU690925B2 (de) |
BG (1) | BG62363B1 (de) |
BR (1) | BR1100329A (de) |
CA (2) | CA2462061A1 (de) |
CY (2) | CY2219B1 (de) |
CZ (1) | CZ286069B6 (de) |
DE (2) | DE10399022I2 (de) |
DK (1) | DK0719278T3 (de) |
EE (1) | EE03241B1 (de) |
ES (1) | ES2113127T3 (de) |
FI (1) | FI115216B (de) |
GR (1) | GR3026144T3 (de) |
HK (1) | HK1004334A1 (de) |
HR (1) | HRP940563B1 (de) |
HU (1) | HU220060B (de) |
IL (1) | IL110978A (de) |
IS (1) | IS1713B (de) |
LU (1) | LU91027I2 (de) |
MY (1) | MY119778A (de) |
NL (1) | NL300122I2 (de) |
NO (2) | NO306117B1 (de) |
NZ (1) | NZ274642A (de) |
OA (1) | OA10575A (de) |
PE (1) | PE15095A1 (de) |
PL (1) | PL180002B1 (de) |
RO (1) | RO117455B1 (de) |
RU (1) | RU2140926C1 (de) |
SA (1) | SA94150231B1 (de) |
SG (1) | SG52650A1 (de) |
SI (1) | SI0719278T1 (de) |
SK (1) | SK281869B6 (de) |
TW (1) | TW369521B (de) |
WO (1) | WO1995007927A1 (de) |
ZA (2) | ZA947118B (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2050436A1 (de) | 2007-12-21 | 2009-04-22 | Siegfried Generics International AG | Pharmazeutische Zubereitungen die Dutasteride enthalten |
Families Citing this family (75)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993023051A1 (en) * | 1992-05-20 | 1993-11-25 | Merck & Co., Inc. | New 17-ester, amide, and ketone derivatives of 3-oxo-4-azasteroids as 5a-reductase inhibitors |
AU5323694A (en) * | 1992-10-06 | 1994-04-26 | Merck & Co., Inc. | 17beta -carboxanilides of 4-aza-5alpha-androstan-3-ones as 5alpha-reductase inhibitors |
TW408127B (en) * | 1993-09-17 | 2000-10-11 | Glaxo Inc | Androstenones |
TW382595B (en) * | 1993-10-15 | 2000-02-21 | Merck & Co Inc | Pharmaceutical composition for use in arresting and reversing androgenic alopecia |
US5547957A (en) | 1993-10-15 | 1996-08-20 | Merck & Co., Inc. | Method of treating androgenic alopecia with 5-α reductase inhibitors |
EP0724592B1 (de) * | 1993-10-21 | 1999-01-07 | Merck & Co. Inc. | 16-substituierte-4-aza-androstan-5-alpha-reduktase-isozym-i-inhibitoren |
US5817818A (en) * | 1994-09-16 | 1998-10-06 | Glaxo Wellcome Inc. | Androstenones |
US6001844A (en) * | 1995-09-15 | 1999-12-14 | Merck & Co., Inc. | 4-Azasteroids for treatment of hyperandrogenic conditions |
US5872126A (en) * | 1996-09-06 | 1999-02-16 | Merck & Co., Inc. | Methods and compositions for treating preterm labor |
US5935968A (en) | 1997-03-17 | 1999-08-10 | Merck & Co., Inc. | Methods for treating polycystic ovary syndrome |
GB9717428D0 (en) * | 1997-08-19 | 1997-10-22 | Glaxo Group Ltd | Pharmaceutical composition |
JP2001521000A (ja) * | 1997-10-28 | 2001-11-06 | メルク エンド カムパニー インコーポレーテッド | 誘発性急性閉尿の予防 |
HUP0101809A3 (en) * | 1998-03-11 | 2002-07-29 | Endorech Inc Sainte Foy | Inhibitors of type 5 and type 3 17betha-hydroxysteroid dehydrogenase and methods for their use |
EP1321146A3 (de) * | 1998-03-11 | 2004-06-02 | Endorecherche Inc. | Typ 5 und Typ 3 17 Beta-Hydroxisteroid-Dehydrogenasehemmer und Verfahren zu ihrer Anwendung |
US5998427A (en) * | 1998-05-14 | 1999-12-07 | Glaxo Wellcome Inc. | Androstenones |
AU4701299A (en) * | 1998-06-23 | 2000-01-10 | Stuart R. Adler | Therapeutic applications of estrogenic carboxylic acids |
US6410565B1 (en) | 1999-02-03 | 2002-06-25 | Eli Lilly And Company | α1-adrenergic receptor antagonists |
AU777770C (en) | 1999-05-04 | 2005-11-10 | Strakan International Limited | Androgen glycosides and androgenic activity thereof |
US6645974B2 (en) | 2001-07-31 | 2003-11-11 | Merck & Co., Inc. | Androgen receptor modulators and methods for use thereof |
AU2002331916B2 (en) * | 2001-10-03 | 2008-07-24 | Merck Sharp & Dohme Corp. | Androstane 17-beta-carboxamides as androgen receptor modulators |
DE60317626T2 (de) * | 2002-01-25 | 2008-10-23 | Asahi Glass Co., Ltd. | Verfahren zur herstellung von 2,5-bis(trifluormethyl)nitrobenzol |
BR0309435A (pt) | 2002-04-24 | 2005-02-15 | Boehringer Ingelheim Pharma | Combinação farmacêutica para o tratamento de hiperplasia prostática benigna ou para a prevenção a longo prazo de retenção urinária aguda |
AU2003223754B2 (en) * | 2002-04-30 | 2007-08-16 | Merck Sharp & Dohme Corp. | 4-azasteroid derivatives as androgen receptor modulators |
US7326717B2 (en) * | 2003-05-06 | 2008-02-05 | L'oreal | Pyrimidine n-oxide compounds for stimulating the growth of keratin fibers and/or reducing loss thereof |
US7022854B2 (en) * | 2003-07-17 | 2006-04-04 | Dr. Reddy's Laboratories, Limited | Forms of dutasteride and methods for preparation thereof |
US20050059692A1 (en) * | 2003-09-09 | 2005-03-17 | Dr. Reddy's Laboratories Limited | Process for the preparation of 17beta-N-[2,5-bis(trifluoromethyl)phenyl] carbamoyl-4-aza-5-alpha-androst-1-en-3-one |
WO2005092341A1 (en) * | 2004-03-22 | 2005-10-06 | Ranbaxy Laboratories Limited | Combination therapy for lower urinary tract symptoms |
EP2305352A1 (de) | 2004-04-02 | 2011-04-06 | Merck Sharp & Dohme Corp. | 5-alpha-Reduktaseinhibitoren zur Behandlung von Stoffwechsel- und anthropometrischen Störungen |
AU2005280334A1 (en) * | 2004-08-25 | 2006-03-09 | Merck Sharp & Dohme Corp. | Androgen receptor modulators |
EP1824495A2 (de) * | 2004-12-03 | 2007-08-29 | ProteoSys AG | Finasterid, dutasterid und zugehörige verbindungen zur vorbeugung/behandlung neurologisch assoziierter störungen |
US20060193804A1 (en) * | 2005-02-24 | 2006-08-31 | L'oreal | Haircare use of cyclic amine derivatives |
AU2006229840B2 (en) * | 2005-03-25 | 2010-12-23 | Merck Sharp & Dohme Corp. | Method of treating men with testosterone supplement and 5alpha-reductase inhibitor |
WO2007120263A2 (en) * | 2005-11-10 | 2007-10-25 | Dr. Reddy's Laboratories Ltd. | Preparation of dutasteride |
EP1897533A1 (de) * | 2006-09-08 | 2008-03-12 | Revotar Biopharmaceuticals AG | Verwendung von 1,6-Bis[3-(3-carboxymethylphenyl)-4-(2-alpha-D-mannopyranosyl-oxy)-phenyl]hexan zur Herstellung von kosmetischen Zusammensetzungen |
EP1946756A1 (de) * | 2007-01-17 | 2008-07-23 | Revotar Biopharmaceuticals AG | Verwendung von Entacapon für kosmetische, dermatologische und pharmazeutische Zusammensetzungen |
FR2920309B1 (fr) | 2007-08-28 | 2010-05-28 | Galderma Res & Dev | Utilisation de travoprost pour traiter la chute des cheveux |
US20090076057A1 (en) * | 2007-09-13 | 2009-03-19 | Protia, Llc | Deuterium-enriched dutasteride |
AR070313A1 (es) * | 2008-01-03 | 2010-03-31 | Gador Sa | Un procedimiento para preparar una forma solida y cristalina de dutasteride, una forma polimorfica del compuesto (forma iii) y una composicion farmaceutica que incluye dicha forma |
FR2929118B1 (fr) | 2008-03-28 | 2010-05-07 | Oreal | Utilisation de l'association de madecassoside et/ou de terminoloside et d'une arginine pour induire et/ou stimuler la croissance de ces fibres keratiniques humaines et/ou freiner leur chute |
FR2929117B1 (fr) | 2008-03-28 | 2010-05-07 | Oreal | Utilisation de l'association du 2,4-diaminopyrimidine 3-n-oxyde et du madecassosside et/ou du terminoloside pour induire et/ou stimuler la croissance de ces fibres keratiniques humaines et/ou freiner leur chute |
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CN101759762B (zh) * | 2008-11-06 | 2013-03-20 | 天津金耀集团有限公司 | 4ad在制备度他雄胺中的应用 |
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FR2949052B1 (fr) | 2009-08-13 | 2015-03-27 | Oreal | Procede de traitement cosmetique du cuir chevelu. |
EP2468262A1 (de) | 2010-12-06 | 2012-06-27 | Krka Tovarna Zdravil, D.D., Novo Mesto | Pharmazeutische Zusammensetzung mit Dutasterid |
BRPI1103204A2 (pt) * | 2011-06-03 | 2014-02-25 | Eurofarma Lab S A | Composição farmacêutica para o tratamento de hiperplasia prostática benigna |
HU230730B1 (hu) | 2011-06-30 | 2017-12-28 | Richter Gedeon Nyrt | Eljárás (5alfa,17béta)-N-[2,5-bisz-(trifluormetil)-fenil]-3-oxo-4-aza-5-androszt-1-én-17-karbonsavamid előállítására |
CN103059098B (zh) * | 2011-10-24 | 2015-04-01 | 成都国为医药科技有限公司 | 一种度他雄胺的制备方法 |
US9622981B2 (en) | 2011-11-17 | 2017-04-18 | Mylan Inc. | Liquid-filled hard gel capsule pharmaceutical formulations |
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AU2014342811B2 (en) | 2013-10-15 | 2019-01-03 | Board Of Regents Of The University Of Texas System | Compositions and methods of modulating short-chain dehydrogenase activity |
ES2555485T1 (es) | 2014-05-26 | 2016-01-04 | Galenicum Health S.L. | Composiciones farmacéuticas que contienen un agente activo |
KR101590072B1 (ko) | 2014-12-23 | 2016-01-29 | 한미약품 주식회사 | 두타스테라이드를 포함하는 자가유화 약물전달 시스템용 조성물 |
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